Top Chief Of Staff Jobs in Chicago, IL

The Principal, Marketing Chief of Staff leads RFPs, manages marketing budgets, tracks agency performance, and supports executive meetings and presentations.

Trusted, high-leverage advisor to the Chief People and Administration Officer and executive team who drives the executive operating system. Owns Board material preparation and cadence, coordinates cross-functional initiatives, frames decisions with data and stakeholders, and leads high-priority work from analysis through execution. Builds operating rhythms, improves communication and accountability, forms focused teams for urgent priorities, and removes friction to increase organizational effectiveness as the company scales.

Partner with the CPO and CTO to run R&D operations: lead operating cadence, OKR alignment, reporting/dashboards, budget governance, and cross-functional strategic initiatives. Triage escalations, drive org design and AI-operating-model projects, and draft executive and board communications to enable prioritized, data-driven R&D decision making.

Serve as the CEO's right-hand, managing their time and communications, driving strategic planning, owning cross-functional projects, building accountability systems, drafting executive materials, and executing organizational priorities to ensure follow-through and operational efficiency.

Lead CEO office operating rhythm, coordinate executive priorities, prepare CEO/board materials, manage performance reviews and dashboards, drive cross‑functional execution, and support high‑impact communications and events.

Senior strategic leader supporting fundraising, operations, and organizational initiatives for Medicine and Biological Sciences Development. Manages major gifts portfolio, teams (up to 30 staff), research/analytics, donor relations, outreach, and marketing. Drives affiliate and international fundraising, partners with senior leadership and trustees, represents the Vice President, and leads campaign execution, special projects, prospect cultivation, solicitation, and stewardship to meet ambitious philanthropic goals.

Provide executive-level administrative support to the CTO and manage day-to-day operations of the Chicago office. Responsibilities include complex calendar management, meeting logistics, office facilities and vendor coordination, onboarding support, expense reporting via Concur, and creating/editing presentations and correspondence using Microsoft Office and AI tools.

The Chief of Staff will lead AI transformation projects, manage investment funds, drive sales initiatives, and oversee client project delivery, requiring self-direction and proactivity.

The Chief of Staff will oversee operational projects, refine strategies, and support leadership in a fast-paced scaling environment.

The Chief of Staff will lead strategic initiatives for new business lines at Atticus, focusing on client acquisition and operational strategy while collaborating with various leaders.

Support co-founders and VP of People with executive logistics, meeting operations, travel coordination, interview and People-team support, culture programming, and ad hoc operational projects. Drive process improvements, vendor coordination, and documentation across a fast-growing healthtech startup.

The Chief of Staff will support the CTO by translating company strategy into operational systems, managing projects, driving alignment, and enhancing leadership within the Tech organization, ensuring effective execution of strategic initiatives.

Serve as a trusted operational partner to a founder, owning business and personal projects end-to-end. Translate high-level goals into scopes, timelines, budgets, and action plans; oversee property buildouts; manage contractors, vendors, advisors, and content/travel logistics; establish systems, provide concise project updates, and protect confidential information with discretion.

Serve as CIOs trusted advisor to translate technology strategy into priorities, operating plans, and measurable outcomes. Own operating model, governance, and executive coordination. Lead cross-functional initiatives, separation readiness, KPIs and dashboards, financial and resource planning, and executive communications to ensure disciplined execution.

Serve as liaison between senior leadership and staff to drive strategic initiatives, oversee daily operations, track project deliverables, develop action plans, manage communications, and organize business-critical meetings while improving operational efficiency.

Trusted advisor to the CVP who runs day-to-day business operations, drives strategy execution and budgeting, orchestrates rhythm of business, leads commercial and operations teams, champions AI/Copilot adoption, manages executive communications, and runs cross-organizational programs to improve organizational health and drive results.

Lead commercial strategy across sales, marketing, and business development to drive revenue growth, market expansion, strategic partnerships, pricing, and go-to-market execution. Oversee teams, financial planning, and performance metrics while mentoring staff and aligning commercial operations with company goals.

Partner with the CEO to design AI-first operating systems, drive cross-functional strategic execution, build board and investor narratives, lead AI transformation across functions, and ensure leadership alignment and measurable outcomes at scale.

Senior strategic partner to the CCMO who drives cross-functional delivery, runs leadership cadence and governance, translates strategy into priorities, manages confidential high‑impact projects, shapes executive engagements, and ensures accountability across Brand, Communications, Marketing and Operations.

Partner with the VP of Operations and executive team to turn strategy into execution: run company planning (OKRs), operating cadence, KPIs, SOC 2 readiness, acquisition integration, investor/vendor relations, recruiting loops, and cross-functional initiatives while driving AI adoption and scaling processes.

Act as the founders' right hand to operationalize AI: prototype internal AI workflows, turn experiments into company-wide programs, run executive cadence and OKRs, unblock cross-functional projects, prepare strategic briefs, enforce responsible AI guardrails, and drive exit-readiness and organizational health.

Serve as the executive owner for AI transformation at mid-market clients: convene and facilitate C-suite AI steering committees, build board-ready AI roadmaps tied to KPIs and ROI, coordinate delivery teams, unblock workstreams, surface expansion opportunities, and refine the AI Chief of Staff playbook to scale Pragmatico’s offerings.

Serve as the CEOs strategic advisor and operational leader, establishing executive cadence, driving cross-functional initiatives, tracking company priorities, managing investor and board relationships, supporting financing, and leading government relations, partnerships, and community engagement to enable national mill deployments and organizational scale.

The Chief of Staff will support the Managing Director of AI, leading AI transformation initiatives, designing automated systems, and ensuring successful delivery across multiple client projects.

Coach and mentor clients pursuing chief of staff and executive support roles. Teach strategic planning, executive support, and AI fundamentals/automation. Provide career guidance including resume, LinkedIn, cover letters, interview prep, networking, salary negotiation, and promotion strategy. Host virtual sessions on flexible schedule and collaborate with Leland team to ensure high-quality client outcomes.